US4355049A - Flavoring with 2-(α-mercaptoalkyl)-3-thiazoline - Google Patents

Flavoring with 2-(α-mercaptoalkyl)-3-thiazoline Download PDF

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Publication number
US4355049A
US4355049A US06/290,624 US29062481A US4355049A US 4355049 A US4355049 A US 4355049A US 29062481 A US29062481 A US 29062481A US 4355049 A US4355049 A US 4355049A
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US
United States
Prior art keywords
foodstuff
thiazoline
flavor
flavoring
parts per
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Expired - Lifetime
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US06/290,624
Inventor
Marcia D. Spencer
Thomas H. Parliment
Denise A. Giordano
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General Foods Corp
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General Foods Corp
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Priority to US06/290,624 priority Critical patent/US4355049A/en
Assigned to GENERAL FOODS CORPORATION, A CORP. OF reassignment GENERAL FOODS CORPORATION, A CORP. OF ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: GIORDANO, DENISE A., PARLIMENT, THOMAS H., SPENCER, MARCIA D.
Priority to EP82305444A priority patent/EP0105988B1/en
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Publication of US4355049A publication Critical patent/US4355049A/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D277/10—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/205—Heterocyclic compounds
    • A23L27/2056—Heterocyclic compounds having at least two different hetero atoms, at least one being a nitrogen atom
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/26—Meat flavours

Definitions

  • This invention relates to a composition which imparts or enhances the flavor of foodstuffs. More particularly a flavoring composition is discovered which imparts or enhances the meaty, sauteed onion flavor, character and aroma of foodstuffs. A process is also disclosed for preparing this flavoring composition.
  • this invention involves adding as a flavoring composition an effective amount of either 2,4-dimethyl-2-(mercaptomethyl)-3-thiazoline or 2,4,5-trimethyl-2-( ⁇ -mercaptoethyl)-3-thiazoline to foodstuffs to impart or enhance a meaty, sauteed onion flavor and aroma in the foodstuffs.
  • the flavoring composition is prepared by reacting 3-mercapto-2-butanone or mercaptoacetone in the presence of ammonia, ethanol and water.
  • This invention is directed to a flavoring composition which provides unique flavor characteristics to foods.
  • the flavoring composition is 2-( ⁇ -mercaptoalkyl)-3-thiazoline and has the following structure: ##STR1## wherein R 1 is either hydrogen or a methyl group.
  • the flavor which this composition imparts is described as a meaty, sauteed onion flavor. This flavor is similar to that obtained upon braising a piece of beef with onions, i.e. a browned meaty flavor with a savory, oniony background (browned onion character).
  • the flavoring composition is specific to the two above identified compounds to impart the desired flavor and aroma. Higher alkyl substitutions have resulted in substantially different flavors and aromas.
  • This flavoring composition can be effectively used in any one of a number of foodstuffs such as sauces, gravies, seasonings, soups, meat analogs or beverages.
  • the level at which the flavoring compound is effective in foodstuffs is generally within the range of 0.05 to 50 parts per million, preferably 0.1 to 10 parts per million of the foodstuff.
  • a unique method of preparing the flavoring composition involves reacting either 3-mercapto-2-butanone or mercaptoacetone in the presence of ammonia (NH 3 ), ethanol and water. More specifically 2,4,5-trimethyl-2-( ⁇ -mercaptoethyl)-3-thiazoline has been prepared as follows: to 1 ml. of water and 3 ml. of 29% aqueous NH 3 adding dropwise a solution of 1.04 gms of 3-mercapto-2-butanone and 1.04 gms of ethanol (95%); stirring the mixture for one hour at room temperature; then extracting the flavoring compound with ether; concentrating on a rotary evaporator and purifying by gas chromatography or distillation.
  • NH 3 ammonia
  • 2,4,5-trimethyl-2-( ⁇ -mercaptoethyl)-3-thiazoline has been prepared as follows: to 1 ml. of water and 3 ml. of 29% aqueous NH 3 adding dropwise a solution of 1.04
  • the flavoring composition 2,4-dimethyl-2-(mercaptomethyl)-3-thiazoline has been prepared as follows: to 1 ml. of water and 3 ml. of 29% aqueous NH 3 buffered to a pH of 7 adding dropwise a solution of 1 gm of mercaptoacetone and 1 gm of ethanol (95%); stirring the mixture for one hour at room temperature; then extracting the flavoring compound with ether; concentrating on a rotary evaporator and purifying by gas chromatography or distillation.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Seasonings (AREA)

Abstract

A flavoring composition of 2-(α-mercaptoalkyl)-3-thiazoline when added to foodstuffs imparts or augments a meaty, sauteed onion flavor and aroma.

Description

BACKGROUND OF THE INVENTION
This invention relates to a composition which imparts or enhances the flavor of foodstuffs. More particularly a flavoring composition is discovered which imparts or enhances the meaty, sauteed onion flavor, character and aroma of foodstuffs. A process is also disclosed for preparing this flavoring composition.
SUMMARY OF THE INVENTION
Briefly, this invention involves adding as a flavoring composition an effective amount of either 2,4-dimethyl-2-(mercaptomethyl)-3-thiazoline or 2,4,5-trimethyl-2-(α-mercaptoethyl)-3-thiazoline to foodstuffs to impart or enhance a meaty, sauteed onion flavor and aroma in the foodstuffs. The flavoring composition is prepared by reacting 3-mercapto-2-butanone or mercaptoacetone in the presence of ammonia, ethanol and water.
DETAILED DESCRIPTION OF THE INVENTION
This invention is directed to a flavoring composition which provides unique flavor characteristics to foods. The flavoring composition is 2-(α-mercaptoalkyl)-3-thiazoline and has the following structure: ##STR1## wherein R1 is either hydrogen or a methyl group.
The flavor which this composition imparts is described as a meaty, sauteed onion flavor. This flavor is similar to that obtained upon braising a piece of beef with onions, i.e. a browned meaty flavor with a savory, oniony background (browned onion character). The flavoring composition is specific to the two above identified compounds to impart the desired flavor and aroma. Higher alkyl substitutions have resulted in substantially different flavors and aromas.
This flavoring composition can be effectively used in any one of a number of foodstuffs such as sauces, gravies, seasonings, soups, meat analogs or beverages. The level at which the flavoring compound is effective in foodstuffs is generally within the range of 0.05 to 50 parts per million, preferably 0.1 to 10 parts per million of the foodstuff.
A unique method of preparing the flavoring composition is also described. Basically it involves reacting either 3-mercapto-2-butanone or mercaptoacetone in the presence of ammonia (NH3), ethanol and water. More specifically 2,4,5-trimethyl-2-(α-mercaptoethyl)-3-thiazoline has been prepared as follows: to 1 ml. of water and 3 ml. of 29% aqueous NH3 adding dropwise a solution of 1.04 gms of 3-mercapto-2-butanone and 1.04 gms of ethanol (95%); stirring the mixture for one hour at room temperature; then extracting the flavoring compound with ether; concentrating on a rotary evaporator and purifying by gas chromatography or distillation.
The flavoring composition 2,4-dimethyl-2-(mercaptomethyl)-3-thiazoline has been prepared as follows: to 1 ml. of water and 3 ml. of 29% aqueous NH3 buffered to a pH of 7 adding dropwise a solution of 1 gm of mercaptoacetone and 1 gm of ethanol (95%); stirring the mixture for one hour at room temperature; then extracting the flavoring compound with ether; concentrating on a rotary evaporator and purifying by gas chromatography or distillation.
When 2,4,5-trimethyl-2-(α-mercaptoethyl)-3-thiazoline was added at levels of 0.1 ppm and 1 ppm to a beef gravy or a chicken gravy a more meaty, sauteed onion flavor and aroma was imparted to the gravies. When 2,4-dimethyl-2-(mercaptomethyl)-3-thiazoline was added at levels of 0.1 ppm and 1 ppm to a beef gravy a savory, browned meat flavor and aroma was imparted to the gravy.

Claims (8)

What is claimed:
1. A process for imparting or enhancing a flavor in a foodstuff comprising adding an amount of a flavoring composition chosen from the group consisting of 2,4-dimethyl-2-(mercaptomethyl)-3-thiazoline and 2,4,5-trimethyl-2-(α-mercaptoethyl)-3-thiazoline, to the foodstuff effective to augment or impart a meaty, sauteed onion flavor.
2. Process of claim 1 wherein the effective amount is within the range of 0.05 to 50 parts per million of the foodstuff.
3. Process of claim 2 wherein the effective amount is within the range of 0.1 to 10 parts per million of the foodstuff.
4. Process of claim 1 wherein the foodstuff is chosen from the group consisting of soup, sauce, seasoning, gravy, meat analog or beverage.
5. A foodstuff comprising an amount of a flavoring composition chosen from the group consisting of 2,4-dimethyl-2-(mercaptomethyl)-3-thiazoline and 2,4,5-trimethyl-2-(α-mercaptoethyl)-3-thiazoline effective to impart or enhance a meaty, sauteed onion flavor in the foodstuff.
6. Foodstuff of claim 5 wherein the effective amount is within the range of 0.05 to 50 parts per million of the foodstuff.
7. Foodstuff of claim 6 wherein the effective amount is within the range of 0.1 to 10 parts per million of the foodstuff.
8. Foodstuff of claim 7 wherein the foodstuff is chosen from the group consisting of soup, sauce, gravy, meat analog or beverage.
US06/290,624 1981-08-06 1981-08-06 Flavoring with 2-(α-mercaptoalkyl)-3-thiazoline Expired - Lifetime US4355049A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US06/290,624 US4355049A (en) 1981-08-06 1981-08-06 Flavoring with 2-(α-mercaptoalkyl)-3-thiazoline
EP82305444A EP0105988B1 (en) 1981-08-06 1982-10-13 Flavoring with 2-(alpha-mercaptoalkyl)-3-thiazoline

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US06/290,624 US4355049A (en) 1981-08-06 1981-08-06 Flavoring with 2-(α-mercaptoalkyl)-3-thiazoline

Publications (1)

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US4355049A true US4355049A (en) 1982-10-19

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EP (1) EP0105988B1 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2289351B1 (en) * 2009-09-01 2013-10-09 International Flavors & Fragrances Inc. Use of thiazoline compounds in flavor applications

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4067344A (en) * 1976-10-07 1978-01-10 International Flavors & Fragrances Inc. Novel tobacco product comprising one or more thiazolines and process
US4243688A (en) * 1979-12-05 1981-01-06 International Flavors & Fragrances Inc. Flavoring with 2-substituted-4,5-dimethyl-Δ3 -thiazolines
US4256776A (en) * 1979-03-05 1981-03-17 International Flavors & Fragrances Inc. Flavoring with certain 2-alkyl-4,5-dialkyl-Δ3 -thiazolines
US4263332A (en) * 1979-03-05 1981-04-21 International Flavors & Fragrances Inc. Use of 2(2'-methylthiopropyl)-4,5-dimethyl-Δ3 -thiazoline to augment or enhance the aroma or taste of mashed potato flavor or mashed potato flavored foodstuffs

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE785657A (en) * 1971-06-30 1973-01-02 Givaudan & Cie Sa NEW AROMATIC COMPOUNDS
CH575402A5 (en) * 1972-09-08 1976-05-14 Givaudan & Cie Sa

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4067344A (en) * 1976-10-07 1978-01-10 International Flavors & Fragrances Inc. Novel tobacco product comprising one or more thiazolines and process
US4256776A (en) * 1979-03-05 1981-03-17 International Flavors & Fragrances Inc. Flavoring with certain 2-alkyl-4,5-dialkyl-Δ3 -thiazolines
US4263332A (en) * 1979-03-05 1981-04-21 International Flavors & Fragrances Inc. Use of 2(2'-methylthiopropyl)-4,5-dimethyl-Δ3 -thiazoline to augment or enhance the aroma or taste of mashed potato flavor or mashed potato flavored foodstuffs
US4243688A (en) * 1979-12-05 1981-01-06 International Flavors & Fragrances Inc. Flavoring with 2-substituted-4,5-dimethyl-Δ3 -thiazolines

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Publication number Publication date
EP0105988B1 (en) 1985-12-27
EP0105988A1 (en) 1984-04-25

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